Donald Trump And Barack Obama's Past Praise Of Diddy Is So Awkward Now

The following article contains references to sexual abuse.

Allegations of misconduct and sexual abuse in the entertainment industry are, sadly, not uncommon. Yet even by those standards, the scandal surrounding Sean "Diddy" Combs is beyond vile. The Grammy-winning rapper was arrested in September 2024 on multiple federal charges, including sexual assault and using his lucrative enterprise to facilitate sex trafficking. Diddy also allegedly coerced, bribed, drugged, and threatened women to engage in sex acts with male sex workers at so-called "Freak Off" hotel parties. He pled not guilty to the multiple charges detailed in the stunning 14-page indictment. Fellow celebs responded either with it's-about-time reactions or no-comment remarks, with those who praised him in the past likely regretting it. 

Among them are two past presidents: Donald Trump and Barack Obama. Both knew the artist back in his Puff Daddy/P. Diddy days, and notably, neither man was occupying the Oval Office at the time. Still, being connected in any way to someone facing 15+ years in jail — or even a life sentence — makes for especially bad optics. These days, Trump is trying to present himself as a devoted family man, perhaps in part to help the public forget his past friendship with the artist. And as a supporter of Kamala Harris's history-making 2024 presidential campaign, Obama would be smart to avoid any hint of association with the disgraced rapper too. Alas, the internet is unforgiving, and there's plenty of proof both men were friendly with Diddy prior to his arrest.

If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673) or go to https://www.rainn.org/.

"I'm Barack Obama; I'm the U.S. Senate candidate from the state of Illinois." That was how a then-unknown political upstart introduced himself to the MTV audience, courtesy of guest interviewer Sean Combs (via YouTube). It was the 2004 Democratic National Convention, and at the time, not one of the 100 Senate members was Black. As Diddy pointed out, "This is a big deal." The two men proceeded to discuss the importance of encouraging young and minority voters to head to the polls with Obama enthusing, "You're a motivating force for young people all across the country. Your music moves people. You're a trendsetter. But part of what we're trying to do is to make sure we're setting a trend in terms of political participation." He also explained to viewers how voting could influence their future.

In an eerily prescient statement, Diddy told the senatorial candidate, "When you want to be the president of the United States, you call your man." Patting his chest, he added, "You call MTV. We're going to give you a platform. We're going to give you a way to speak, because you're on to something, kid! You're on to something! You're making sense to me." 

Sure enough, Obama won the Senate seat in 2005, and three years later, he began his run for the White House. Combs attended at least one Democratic rally in Florida, along with Ben Affleck, Hillary Clinton, and several others. The hip-hop mogul's support no doubt helped Obama nab his history-making win, but all things considered, he might not want to be reminded of that uncomfortable fact.

Long before he was describing himself as "your favorite president," Donald Trump was merely a real-estate mogul and bestselling author. Being based in Manhattan afforded him the opportunity to rub elbows with tons of celebs, including Sean "Diddy" Combs. The two men were often photographed together attending social events, including at Combs' 29th birthday party. Trump later wed Melania Knauss and became a TV star as the host of "The Apprentice," while Diddy continued releasing hit songs, producing other people's music, and starring in his own hit reality show, "Making the Band." Still, they remained chummy. 

In fact, Newsweek reports that Trump once referred to the rapper as "the legendary Puff Daddy," while Diddy praised the controversial businessman as "a friend of mine [who] works really hard." But a comment Trump made on "The Celebrity Apprentice" now seems especially unfortunate. One of the contestants was Aubrey O'Day, whose group Danity Kane was made famous through "Making the Band." According to the Daily Mail, Trump proudly told O'Day, "I love Diddy. You know, he's a good friend of mine, he's a good guy. Is he a good guy?" She refused to answer the question, and seemed upset that Trump had even brought up the subject. 

Years later, the singer distanced herself from both the group and Combs, claiming he had made immoral demands of her. The former president, meanwhile, has not only publicly separated himself from his former "friend" since Diddy's shocking arrest, but Trump went a step further and tried to implicate his political opponent in the scandal. Per NBC News, the divisive candidate took to Truth Social to repost a photo of Kamala Harris with Combs, alongside a caption hinting that she might have been involved in the rapper's infamously wild parties. Trump eventually took it down after the pic was proven to be photoshopped.